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Chapter 29: 23P (page 1177)

Devise a synthesis of each peptide from amino acid starting materials:

(a) Leu鈥揤al; (b) Ala鈥揑le鈥揋ly.

Short Answer

Expert verified

The amino acids, Leucine and Valine, exist as shown:

The structure of Leu-Val dipeptide is:

Step by step solution

01

The structure of Leucine and Valine

The amino acids, Leucine and Valine, exist as shown:

The structure of Leu-Val dipeptide is:

02

The synthesis of Leu-Val dipeptide

The synthesis of Leu-Val dipeptide involves the following steps:

  • Protect the amine group in Leucine by reacting with Boc.

  • Protect the carboxylic acid group in -Val as a benzyl ester.

  • Then both are allowed to react to form the required dipeptide in the presence of DCC.

  • In the last step, the protecting groups should be removed.

03

Synthesis of Ala-Ile-Gly

The amine group is protected with Boc(t-butyloxycarbonyl) group, and the carboxylic acid group is protected with benzyl alcohol in the presence of mild acid.

  • First, in Ala, the amine group is protected with Boc.

  • Next, the 鈥揅OOH group in Ile amino acid is protected with benzyl alcohol.

  • Next, these two amino acids are allowed to react with each other then an amide group is formed, a dipeptide of Ala-Ile with protecting groups.

  • The carboxylic acid group in glycine is protected. This amino acid is allowed to react with the dipeptide.

Thus, the required tripeptide will be obtained.

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Most popular questions from this chapter

Question: Draw the other three stereoisomers of L-isoleucine, and label the stereogenic centers as R or S.

For the tetra peptide Asp鈥揂rg鈥揤al鈥揟yr:

a. Name the peptide using one-letter abbreviations.

b. Draw the structure.

c. Label all amide bonds.

d. Label the N-terminal and C-terminal amino acids

Explain why the pKaof the -NH3+group of an 伪-amino acid is lower than the pKaof the ammonium ion derived from a 1掳amine (RNH3+). For example, pKaof the -NH3+group of alanine is 9.87 but the pKaof CH3NH3+is 10.63.

Draw the structure of the N-phenylthiohydantoin formed by initial Edman degradation of each peptide: (a) Ala-Gly-Phe-Phe; (b) Val-Ile-Tyr.

Glutathione, a powerful antioxidant that destroys harmful oxidizing agents in cells, is composed of glutamic acid, cysteine, and glycine, and has the following structure:

a. What product is formed when glutathione reacts with an oxidizing agent?

b. What is unusual about the peptide bond between glutamic acid and cysteine?
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